In October 2013, Premier of Ontario Kathleen Wynne announced government support for expansion of the trail system to better connect the 2015 Pan Am Games venues and community.

"I want to ensure that all of the people of this province benefit from our investments in the Pan Am and Parapan Am Games, because that is how we can grow as One Ontario. Extending our trails system and connecting more communities is a great way for the excitement of the Games to live on well beyond 2015." Kathleen Wynne, Premier of Ontario, October 3rd, 2013[2]

The announcement ensures that "the province will work with First Nation and Métis communities and organizations to incorporate Aboriginal markers along the trails to honour the history and culture of Aboriginal communities in Ontario."

The jewel of the Waterfront Trail lies at the Toronto Islands Ferry Terminal where trail users can catch a ferry to the expansive Toronto Islands including Centre Island and Hanlon's Point Beach. In 2015, the Waterfront Trail is expected to connect to the huge underground Toronto PATH system. Cyclists and skaters are encouraged on the peaceful island where only utility vehicles are permitted.

Among the artistic touches of this portion of the trail include the architecturally renowned Wave Decks, designed by West8.[5]

The Beaches community in eastern Toronto is an important location on the trail, being one of the only neighbourhoods in Toronto with residential homes next to the lakeshore. The Beach itself is a popular destination, hosting games of beach volleyball, and attracting many cyclists and rollerbladers. North of the waterfront are many small stores and restaurants along Queen Street and The Danforth. From the Beaches, the trail, called the Martin Goodman Trail, runs west along the Toronto waterfront for its entire length, with only a few sections on city streets. Currently, there isn't any path running east along the waterfront from the Beaches.

Port Credit straddles the Credit River with a mix of residential and commercial development along the trail. Most of the trail is separated from traffic with the exception of some residential streets at the east end near the Adamson Estate.

Individuals and groups can sometimes be seen performing yoga, T'ai chi and other arts at the public gazebo here. In addition, Spencer Smith Park hosts the annual Sound Of Music festival, a longtime tradition and celebration for Halton and surrounding areas.

In July 2014, the provincial government of Ontario announced a $100 million renovation plan that will see the transformation of Ontario Place from an entertainment venue into a huge mixed-use park that will anchor the trail in this section.[7]

Unlike Quebec's extensive trail system - Route Verte - portions of the trail are inaccessible for safe travel for cyclists. There is an effort by the Waterfront Regeneration Trail, operators of the trail, to expand the cycling portions of the route.

"The Waterfront Regeneration Trail is focused on creating a cycling route around the Great Lakes, and has big expansion plans and dreams for the coming years to increase significantly its mileage. Some of the biggest deterrents for cycle tourists are poor road conditions that force cyclists into traffic and a lack of good signage."[8]